Diglyme

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Diglyme

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Template:Longitem	1736101
ChEBI	Template:Unbulleted list
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EC Number	Template:Unbulleted list
Template:Longitem	26843
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UN number	2252 1993
Template:Longitem	Template:Chem2
Molar mass	Template:Chem molar mass
Density	0.937 g/mL
Melting point	Template:Chembox CalcTemperatures
Boiling point	Template:Chembox CalcTemperatures
Template:Longitem	Diethylene glycol diethyl ether, ethylene glycol dimethyl ether

Diglyme, or bis(2-methoxyethyl) ether, is an organic compound with the chemical formula Template:Chem2. It is a colorless liquid with a slight ether-like odor. It is a solvent with a high boiling point. It is the dimethyl ether of diethylene glycol. The name diglyme is a portmanteau of diglycol methyl ether. It is miscible with water as well as organic solvents.

It is prepared by a reaction of dimethyl ether and ethylene oxide over an acid catalyst.

Solvent

File:(Na(diglyme)2)cation-3D-balls.png

Structure of [Na(diglyme)₂]⁺ as found in its salt with the fluorenyl anion.

Because of its resistance to strong bases, diglyme is favored as a solvent for reactions of alkali metal reagents even at high temperatures. Rate enhancements in reactions involving organometallic reagents, such as Grignard reactions or metal hydride reductions, have been observed when using diglyme as a solvent.

Diglyme is also used as a solvent in hydroboration reactions with diborane.

It serves as a chelate for alkali metal cations, leaving anions more active.

Safety

The European Chemicals Agency lists diglyme as a substance of very high concern (SVHC) as a reproductive toxin.

At higher temperatures and in the presence of active metals diglyme is known to decompose, which can produce large amounts of gas and heat. This decomposition led to the T2 Laboratories reactor explosion in 2007.